Naslov
Ferrocene Compounds. XXXVI. Lipase-catalyzed Enantioselective Acetylation of Prochiral 2-(omega-Ferrocenylalkyl)propane-1, 3-diols

Autori
Đaković, Senka ; Lapić, Jasmina ; Rapić, Vladimir

Izvornik
Biocatalysis and Biotransformation (1024-2422) 21 (2003), 6; 291-295

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ferrocene prochiral diols; biocatalysis; enentioselectivity; lipases

Sažetak
Enantioselective acetylation (desymmetrization) of prochiral 2-(ferrocenylmethyl)propane-1, 2-diol (1), 2-(2-ferrocenylethyl)propane-1, 2-diol (2) and 2-(3-ferrocenylpropyl)propane-1, 2-diol (3) into chiral monoacetates [(+)-4-(+)-6], with a series of microbial lipases in benzene at 27_oC, revealed the lipase from Pseudomonas sp (PSL) as the most selective. Acetylation was fastest and the most enentioselective for conversion 1 to (+)-4 by PSL (97% e.e.). By comparison of the compounds (+)-4-(+)-6 with their benzene analogues of the known (R) absolute configuration, on the basis of their elution orders on Chiracel OD, and the same direction of their optical rotations, an R-configuration is proposed for (+)-monoacetates 4-6.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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